Catalytic Difunctionalization of Alkenes under Visible Light Irradiation: Synthesis of Iminofuranones

Boyu Liu; Guangxian Chen; Lele Zhang; Feiwei Yan; Feiming Li; Zhixiong Cai; Mingqiang Huang; Lina Cai; Shunyou Cai

doi:10.1002/cjoc.202401116

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (7) : 798 -804. DOI: 10.1002/cjoc.202401116

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Catalytic Difunctionalization of Alkenes under Visible Light Irradiation: Synthesis of Iminofuranones

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Abstract

Here, we show a cost-effective and environmentally friendly method for synthesizing iminofuranones using visible light and the photocatalyst 2-bromoanthraquinone. Our approach uses only oxygen as the oxidant, avoiding the need for additional transition metals and strong oxidizing agents. By employing a mixed solvent system of DMF and CHCl ₃ under ambient conditions, we have achieved highly diastereoselective conversions of various 2-vinyl benzamides and alkenyl amides into functionalized iminoisobenzofuranones and iminofuranones. This versatile process is broadly applicable and enables late-stage structural modifications of complex substrates with bioactive moieties.

Keywords

Photocatalysis / Amides / Cyclization / Oxygenation / Radical reactions / Singlet oxygen / Diastereoselectivity / Oxygen heterocycles

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Boyu Liu, Guangxian Chen, Lele Zhang, Feiwei Yan, Feiming Li, Zhixiong Cai, Mingqiang Huang, Lina Cai, Shunyou Cai. Catalytic Difunctionalization of Alkenes under Visible Light Irradiation: Synthesis of Iminofuranones. Chinese Journal of Chemistry, 2025, 43(7): 798-804 DOI:10.1002/cjoc.202401116